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Preston AJ, Fraenkel G, Chow A, et al. Dynamic helical chirality of an intramolecularly hydrogen-bonded bisoxazoline. J Org Chem. 2003;68(1):22-6doi: 10.1021/jo026496f.
Preston, A. J., Fraenkel, G., Chow, A., Gallucci, J. C., & Parquette, J. R. (2003). Dynamic helical chirality of an intramolecularly hydrogen-bonded bisoxazoline. The Journal of organic chemistry, 68(1), 22-6. https://doi.org/10.1021/jo026496f
Preston, Adam J, et al. "Dynamic helical chirality of an intramolecularly hydrogen-bonded bisoxazoline." The Journal of organic chemistry vol. 68,1 (2003): 22-6. doi: https://doi.org/10.1021/jo026496f
Preston AJ, Fraenkel G, Chow A, Gallucci JC, Parquette JR. Dynamic helical chirality of an intramolecularly hydrogen-bonded bisoxazoline. J Org Chem. 2003 Jan 10;68(1):22-6. doi: 10.1021/jo026496f. PMID: 12515456.
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J Org Chem. 2003 Jan 10;68(1):22-6. doi: 10.1021/jo026496f.

Dynamic helical chirality of an intramolecularly hydrogen-bonded bisoxazoline.

The Journal of organic chemistry

Adam J Preston, Gideon Fraenkel, Albert Chow, Judith C Gallucci, Jon R Parquette

Affiliations

  1. Department of Chemistry, The Ohio State University, Columbus, Ohio 43210, USA.

PMID: 12515456 DOI: 10.1021/jo026496f

Abstract

The synthesis and conformational properties of 2,6-bis-[2-((4S)-4-methyl-4,5-dihydro-1,3-oxazol-2-yl)phenyl]carbam oylpyridines, 2, have been described. Bisoxazoline 2a was prepared in five steps from 2-nitrobenzoyl chloride in an overall yield of 71%. In contrast to related structures such as 1, bisoxazoline 2a exhibits a highly biased P-type helical conformation in solution and in the solid state. In the crystal lattice, 2a further assembles into a left-handed helical superstructure aligned along the crystallographic c axis. The barrier to helical interconversion, as measured by line-shape analysis of the temperature-dependent (1)H NMR spectra of thiobenzyl derivative 2b, was determined to be quite low ((Delta)G(++) = 12.3 kcal/mol), indicating the presence of a highly dynamic helical chirality.

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